Triethylamine → HCID 67230608, compound

HRID 1511958Notes

Reaction equation

HRID 1511958 reaction equation
C(OC(=O)[N:7]([CH2:13][CH2:14][CH2:15][CH3:16])[N:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1)(C)(C)C.C(N(CC)CC)C.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C>C(Cl)Cl>[CH2:13]([NH:7][N:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1)[CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 67230193Butyl-pyrrol-1-yl-carbamic acid tert-butyl ester

Product 1

HCID 67230608HCID 67230608, compoundYield 113.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of butyl-pyrrol-1-yl-carbamic acid tert-butyl ester (1.435 g), triethylamine (2.06 mL) and TMSOTf (1.79 mL) in DCM was stirred at rt for 15 min. The mixture was then diluted with DCM, washed with water, saturated sodium chloride solution and then dried over sodium sulfate, filtered, concentrated to give the desired product as oil (943 mg). 1H NMR (CDCl3, δ in ppm): 6.74 (m, 2H), 6.04 (m, 2H), 4.9 (very broad, 1H), 3.11 (t, 2H, J=7.1 Hz), 1.44-1.22 (m, 4H), 0.92 (t, 2H, J=7.3 Hz).

Workup

  1. washwashed with water, saturated sodium chloride solution
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-436aa6da1d964e71bc7d9467d259ad47
Source dataset
uspto-grants-2012_07
Patent number
US08217043B2

Reaction notes

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